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It was one of the city’s more celebrated initiatives: attract food trucks to Boston by staging a contest for the right to operate on City Hall Plaza.

But the Food Truck Challenge offered by Mayor Thomas M. Menino’s administration last year is running into some obstacles just as spring arrives, with one of the three winning contestants backing out and some of the other food truck operators complaining about the city’s bureaucracy.

The former co-owner of World Eats, one of the winning contestants, says his business partnership dissolved after he decided that setting up on City Hall Plaza wouldn’t be economically feasible. He informed officials at a March 2 meeting that he would not set up shop there. World Eats will now be replaced by the fourth-place finisher, Clover Food Lab.

“They way it was proposed originally was that it was for any existing food truck or for a concept that included a future truck. It made you believe it was a very fair contest — that people with or without money could enter and have a chance of winning,’’ said Santiago Lopez, who estimates he spent $2,000 to participate in the challenge. “What you found going forward was that most of these contests made you reach into your pocket and spend some considerable money.’’

The challenge was introduced last summer as part of the city’s approach to fight obesity and promote a healthy life style. The idea was to expand access to fresh fruits and produce, limit the availability of unhealthy foods and sugary drinks, and encourage more physical activity.

In September, operators of about 30 new and existing food trucks applied to claim one of three coveted spots just off Congress Street between City Hall and Faneuil Hall from April 4 to Oct. 31. Contestants produced 60-second promotional videos and went through two rounds of public voting.

In the run-up to the selection of the winners in late fall, the six finalists served free samples and showed off their menus at a daylong taste-testing on City Hall Plaza; more than 500 people showed up.

“The lines just drew on, which is great publicity for City Hall, but that’s a huge cost,’’ said TiffanyPham, who operates Momogoose, another contest winner. “We were not prepared for the crowds that came.’’

The contest website states that winners would receive “technical assistance, permitting guidance, and assistance applying for low-interest loans from the City of Boston.’’ But contestants say that they haven’t gotten much help finding additional locations to operate in Boston, and they complain that simple requests to the city — from providing extra garbage cans and electricity to allowing tents on the location for inclement weather — were routinely denied.

Edith Murnane, director of food initiatives for the city, said the support for food truck operators is “an ongoing conversation and something that is foremost in pushing us forward.’’ She added that the contest was intended to “get people started or to try something new,’’ the prize being six months of free rent on City Hall Plaza.

Lopez would like the opportunity to expand in the city, but he questions whether the city thought through where less-established food truck operators such as himself would go after the six months ended. Legislation to allow for permits so the trucks could operate on public ways downtown east of Park Drive hasn’t passed, for example.

Similarly, Lopez said he ran into trouble when he tried to expand his reach. When Emerson College showed interest in Lopez operating his truck on Boston Common at the corner of Tremont and Boylston streets, he applied for a permit with Boston’s Department of Parks and Recreation. After a lengthy wait, Lopez’s proposal was rejected in November. The explanation from Paul McCaffrey, permitting director, was that “food trucks are inconsistent with the character of a historic park on a daily basis.’’

Murnane, however, said that Clover Food Lab has just been approved for a spot on Boston Common.

Another truck owner, Asta Schuette, co-owner of Bon Me, said she is glad Boston is taking steps to welcome food trucks, but she also pointed to a “lack of cohesion’’ between departments regarding food truck permitting.

Murnane said she expects legislation addressing some of the permit restrictions to be passed “very soon.’’ Additionally, she said the city will send out a request for information to more than 100 existing or interested truck vendors on their preferences for operating in Boston.

The information will then be used to create “hubs’’ for food trucks throughout the city, and vendors will be able to apply for spaces at one of these spots.

One location where food trucks have been successful is the Rose F. Kennedy Greenway. The Greenway is expanding from one food truck during last year’s pilot vending program to several this year, said Nancy Brennan, executive director of the Rose F. Kennedy Greenway Conservancy.

“We have worked collaboratively with the city throughout this process,’’ she said.

Despite the complaints, Murnane is optimistic about what lies ahead for food trucks.

“I’m excited that food trucks are going to be out on the streets,’’ she said. “When people look at Boston, they’re going to see good, fun, healthy, and sometimes not healthy food trucks out there in a way that helps activate the city.’’